Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 48, No. 2, 1998, pp.285-294
Published online, 1st January, 1970
DOI: 10.3987/COM-97-8053
The Dakin-West Reaction of N-Acyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acids Using Trifluoroacetic Anhydride: Structural Revision for the Unexpected Product

Masami Kawase,* Youichi Okada, and Hiroshi Miyamae

*Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japana


The Dakin-West reaction of N-pivaloyl- and N-benzoyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acids (1a-e) with trifluoroacetic anhydride yielded unexpectedly 1-(1-acyloxy-2,2,2-trifluoroethyl)-3,4-dihydroisoquinoline derivatives (3a-e) in good yields. Among of the products (3), the structure of 3b has been confirmed by X-Ray crystallography. The carbamate derivatives (1h, i) gave 1-trifluoroacetyl-N-acyl-1,2,3,4-tetrahydroisoquinolines (4e, f), the Dakin-West reaction products, as a main product. The reaction of N-acetyl derivative (1g) produced completely different type of the product (5).